Collect. Czech. Chem. Commun. 2011, 76, 1549-1566
Published online 2011-12-22 13:10:35

Conformationally locked nucleoside analogues based on the bridgehead substituted 7-oxonorbornane and their antiviral properties

Milan Dejmeka, Hubert Hřebabeckýa, Martin Dračínskýa, Johan Neytsb, Pieter Leyssenb, Helena Mertlíková-Kaiserováa and Radim Nenckaa,*

a Gilead Sciences & IOCB Research Centre, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Rega Institute for Medical Research, Minderbroedersstraat 10, BE-3000 Leuven, Belgium


We report on the preparation of novel 1′-homonucleoside derivatives locked in a West conformation by 1′,4′-bridge consisting of annulated benzene or naphthalene ring. The crucial step of the synthesis was Diels–Alder reaction of an appropriate aryne with a suitable furane derivative. Antiviral properties of novel compounds were studied and slight activity against HCV was detected in several compounds.

Keywords: 1′-Homonucleosides; Diels–Alder reaction; Cycloaddition; Antiviral agents.

References: 16 live references.